Hydrochloric Acid → HCID 58877658, compound

HRID 2118204Notes

Reaction equation

HRID 2118204 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=2)=[C:10](\[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[CH:11]=[CH2:12])=[CH:5][CH:4]=1.[OH-].[Na+].Cl.O>CCO.C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[C:9](/[C:19]2[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=2)=[C:10](\[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[CH2:11][CH3:12])=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86612488HCID 86612488, compound

Product 1

HCID 58877658HCID 58877658, compoundYield 106%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 5 (39.80 g, 96.5 mmol) was dissolved in EtOH (300 mL) and THF (300 mL). 1 M aqueous NaOH (250 mL, 250 mmol) was added and the solution refluxed for 2 h. The reaction was cooled to RT and then acidified to pH 2 with 6N aq. HCl. H2O (750 mL) and CH2Cl2 (500 mL) were added and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organics were dried (Na2SO4) and concentrated to provide the title compound, 6 (39.34 g, 100%), as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 0.95 (t, J=7.4 Hz, 3H), 2.48 (q, J=7.4 Hz, 2H), 3.69 (s, 3H), 6.46 (d, J=15.8 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 6.77 (d, J=8.6 Hz, 2H), 7.10-7.12 (m, 3H), 7.13-7.19 (m, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.54 (d, J=8.3 Hz, 2H), 7.80 (d, J=15.8 Hz, 1H).

Workup

  1. temperaturethe solution refluxed for 2 h
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-004561f730484f3fb1b5de8e3270debb
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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